Cesium carbonate → 8-(1-Ethyl-propyl)-3-(3,5-dimethyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226040

반응식

HRID 226040 반응식
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].[CH3:18][C:19]1[C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[S:22][CH:23]=1.[C:28]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN(C=O)C>[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13]([C:23]3[S:22][C:21]4[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:20]=4[C:19]=3[CH3:18])=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2]

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 738173-Methylbenzo[b]thiopheneHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine

생성물 1

HCID 577526068-(1-Ethyl-propyl)-3-(3,5-dimethyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine수율 85%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

A mixture of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.145 mmol), 3-methyl-benzo[b]thiophene (7.25 mmol), Pd2 dba3 (0.0072 mmol), triphenylphosphine (0.029 mmol), and cesium carbonate (0.29 mmol) in previously degassed DMF (0.5 ml) is added to a pressure tube with a stirring bar. The mixture is degassed for 30 min. After heating for 16 h at 130° C., reaction mixture is cooled, diluted with diethylether and washed with saturated aqueous ammonium chloride solution. The organic layer is dried over anhydrous magnesium sulfate, filtered, and the solvent is removed in vacuo. The residue is purified by silica gel column chromatography using mixtures of hexane-ethyl acetate as eluent to give the title compound (85%).

후처리

  1. additionis added to a pressure tube with a stirring bar
  2. customThe mixture is degassed for 30 min
  3. customreaction mixture
  4. temperatureis cooled
  5. washwashed with saturated aqueous ammonium chloride solution
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed in vacuo
  9. customThe residue is purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ae5b6238cd8747faba4bf0158a24b4f7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

연결된 노트

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